Lactones with Methylcyclohexane Systems Obtained by Chemical and Microbiological Methods and Their Antimicrobial Activity

Molecules

Małgorzata Grabarczyk¹  Katarzyna Wińska¹  Wanda Mၜzka¹  Anna K. Żołnierczyk¹  Barbara ឺrowska²  Mirosᐪw Anioł¹ 

[1] Department of Chemistry, University of Environmental and Life Sciences, Norwida 25, Wrocław 50-375, Poland; E-Mails:;Department of Biotechnology and Food Microbiology, University of Environmental and Life Sciences, Chełmońskiego 37/41, Wrocław 51-630, Poland; E-Mail:

关键词: lactones;    biotransformations;    hydrolytic dehalogenation;    Fusarium species;    antimicrobial activity;   

DOI  :  10.3390/molecules20023335

来源: mdpi

【 摘 要 】

Eight new lactones (δ-chloro-, δ-bromo- and δ-iodo-γ-lactones), each with a methylcyclohexane ring, were obtained by chemical means from (4-methylcyclohex-2-en-1-yl) acetic acid or (6-methylcyclohex-2-en-1-yl) acetic acid. Whole cells of ten fungal strains (Fusarium species, Syncephalastrum racemosum and Botrytis cinerea) were tested on their ability to convert these lactones into other products. Some of the tested fungal strains transformed chloro-, bromo- and iodolactone with a methyl group at C-5 into 2-hydroxy-5-methyl-9-oxabicyclo[4.3.0]nonan-8-one during hydrolytic dehalogenation. When the same lactones had the methyl group at C-3, no structural modifications of halolactones were observed. In most cases, the optical purity of the product was low or medium, with the highest rate for chlorolactone (45.4%) and iodolactone (45.2% and 47.6%). All of the obtained compounds were tested with reference to their smell. Seven halolactones and the hydroxylactone obtained via biotransformation of halolactones with 5-methylcyclohexane ring were examined for their antimicrobial activity. These compounds were capable of inhibiting growth of some bacteria, yeasts and fungi.

【 授权许可】

CC BY   
© 2015 by the authors; licensee MDPI, Basel, Switzerland.